Hydrazine hydrate (1:1) → 2,6-Pyridinedimethanamine

HRID 363357Notes

Reaction equation

HRID 363357 reaction equation
O.NN.C1(=O)[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]3C(=O)C4=CC=CC=C4C3=O)[N:11]=2)C(=O)C2=CC=CC=C12>C(O)C>[NH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH2:17])[N:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10596941HCID 10596941, compound

Product 1

HCID 137237542,6-Pyridinedimethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (2.4 ml, 50 mmol) was added to a solution of 2,6-bis-(phthalimidomethyl)-pyridine (1.99 g, 5.0 mmol) in 95% ethanol (50 ml). The mixture was refluxed for 3 hours. After cooling it was concentrated on a rotary evaporator and the residue was purified by chromatography on silica gel (eluent: methylene chloride/ethanol, 100/2) to give 2,6-bis-(aminomethyl)-pyridine in the form of a yellow oil.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperatureAfter cooling it
  3. concentrationwas concentrated on a rotary evaporator
  4. customthe residue was purified by chromatography on silica gel (eluent: methylene chloride/ethanol, 100/2)

Sources & evidence

ORD record
ord-5e4f132b37894c7e9e72fce13163880e
Source dataset
uspto-grants-1999_02
Patent number
US05874438

Reaction notes

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